m-Chloroperbenzoic acid → 5-(Oxiran-2-yl)-2,1,3-benzoxadiazole

HRID 1502054Notes

Reaction equation

HRID 1502054 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]2=[N:7][O:8][N:9]=[C:5]2[CH:4]=1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[O:20]1[CH2:2][CH:1]1[C:3]1[CH:11]=[CH:10][C:6]2=[N:7][O:8][N:9]=[C:5]2[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 595687205-Ethenyl-2,1,3-benzoxadiazole

Product 1

HCID 595686615-(Oxiran-2-yl)-2,1,3-benzoxadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-ethenyl-2,1,3-benzoxadiazole (1.80 g, 12.3 mmol) in DCM (20 mL) was slowly added m-CPBA (3.8 g, 22 mmol) at 0° C. The flask was warmed to room temperature; the mixture was then stirred for 12 hours. TLC as well as LC indicated that reaction had gone to completion. The mixture was washed with aqueous Na2S2O3, NaHCO3, and water. The organic layers was washed with brine and then concentrated. The residue was purified over silica gel to afford the title compound.

Workup

  1. customat 0° C
  2. customTLC as well as LC indicated that reaction
  3. washThe mixture was washed with aqueous Na2S2O3, NaHCO3, and water
  4. washThe organic layers was washed with brine
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel

Sources & evidence

ORD record
ord-9b1e90322f5a456fb9af78d4c1cf850a
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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